HCID 57526929, compound → HCID 57526954, compound

HRID 1452666Notes

Reaction equation

HRID 1452666 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[CH:9]=[CH:10]/[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[H][H]>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 2

HCID 57526929HCID 57526929, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57526954HCID 57526954, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl (4E)-5-(2-methoxyphenyl)-4-pentenoate (3.40 g, 14.5 mmol) in a mixture of EtOAc and MeOH (40.0/10.0 mL), Pd/C (palladium on carbon 10%, 0.700 g) was added in small portions to avoid fire. The reaction mixture was then stirred for overnight at room temperature under 300 psi of hydrogen. After the pressure was released, the mixture was filtered through Celite and the Celite was washed with EtOAc (3×50 mL). The filtrate was concentrated in vacuo to afford crude product as a light yellow oil (3.40 g 100%), which was used without further purification.

Workup

  1. additionwas added in small portions
  2. filtrationthe mixture was filtered through Celite
  3. washthe Celite was washed with EtOAc (3×50 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-251c56314fdd4ce8a33fbf9146a80cb4
Source dataset
uspto-grants-2009_01
Patent number
US07473698B2

Reaction notes

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